dioctadecyl-N-(3-carboxypropanoyl)-L-glutamate | 125401-64-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dioctadecyl-N-(3-carboxypropanoyl)-L-glutamate
• 英文别名: L-Glutamic acid, N-(3-carboxy-1-oxopropyl)-, 1,5-dioctadecyl ester；4-[[(2S)-1,5-dioctadecoxy-1,5-dioxopentan-2-yl]amino]-4-oxobutanoic acid
• CAS: 125401-64-1
• 化学式: C₄₅H₈₅NO₇
• 分子量: 752.172
• InChiKey: UBJQZCBPVOAIHW-RWYGWLOXSA-N

物化性质

• 熔点：
  82-84 °C
• 沸点：
  799.2±55.0 °C(Predicted)
• 密度：
  0.965±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16.8
• 重原子数：
  53
• 可旋转键数：
  44
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dioctadecyl-N-(3-carboxypropanoyl)-L-glutamate 、 N,N'-[iminobis(trimethylene)]-bis[quinamide] 在 三乙胺 、 氯甲酸异丁酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.5h， 以77%的产率得到
  参考文献：
  名称：

  Preparation of gemini-type amphiphiles bearing cyclitol head groups and their application as high-performance modifiers for lipases

  摘要：

  Five gemini-type amphiphiles bearing cyclitol head groups, which have abundance of axial hydroxy groups, are newly synthesized. The syntheses are based on a common mixed anhydride method utilizing N,N'-[iminobis(trimethylene)]bisquinamide, prepared from iminobispropylamine and quino-1,5-lactone, and dialkyl N-(3-carboxypropanoyl)-L-glutamates as polar and hydrophobic components, respectively. Candida rugosa lipase (CRL) and Pseudomonas cepacia lipase (PCL) are co-lyophilized with these synthesized gemini-type amphiphiles, and their transesterification activities in organic solvents are evaluated. The modified PCL and CRL prepared by using each amphiphile showed highly enhanced and moderately enhanced enzyme activity, respectively. These results are discussed in terms of the increased preferential exclusion of the hydrophilic heads of the amphiphile and of the topological view of the amphiphile. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.12.006
• 作为产物：
  描述：

  硬脂醇 在 potassium carbonate 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 dioctadecyl-N-(3-carboxypropanoyl)-L-glutamate
  参考文献：
  名称：

  Hachisako, Hiroshi; Yamazaki, Tetsuya; Ihara, Hirotaka, Journal of the Chemical Society. Perkin transactions II, 1994, # 7, p. 1671 - 1680

  摘要：

  DOI：

文献信息

• Extraordinary Monomer-Dimer Transition of Methylene Blue Induced by the Phase Transition of Telomer-Bilayer Membranes Formed from Dialkyl L-Glutamate Amphiphiles with Oligo-Acrylic Acid-Head Group
  作者：Hiroshi Hachisako、Yoshiaki Motozato、Ryoichi Murakami、Kimiho Yamada

  DOI：10.1246/cl.1992.219

  日期：1992.2

  L-glutamates with oligo-acrylic acid-head group were prepared. Methylene Blue interacted with these bilayers to form both monomeric and dimeric species. These monomeric species were converted to the dimeric species due to the gel-to-liquid crystalline phase transition of bilayer matrix. A similar phenomenon was observed even in the case of Acridine Orange.

  制备了由具有低聚丙烯酸头基团的 L-谷氨酸二烷基酯形成的新型阴离子调聚物双层。亚甲蓝与这些双层相互作用形成单体和二聚体。由于双层基质的凝胶到液晶相转变，这些单体物质被转化为二聚体物质。即使在吖啶橙的情况下也观察到类似的现象。
• Thermodynamic and structural characterization of amino acid-linked dialkyl lipids
  作者：Stephanie Tristram-Nagle、Ruthven N.A.H. Lewis、Joseph W. Blickenstaff、Michael DiPrima、Bruno F. Marques、Ronald N. McElhaney、John F. Nagle、James W. Schneider

  DOI：10.1016/j.chemphyslip.2004.11.001

  日期：2005.3

  Using differential scanning calorimetry (DSC), X-ray diffraction (XRD) and Fourier transform infrared spectroscopy (FI'IR), we determined some thermodynamic and structural parameters for a series of amino acid-linked dialkyl lipids containing a glutamic acid-succinate headgroup, and di-alkyl chains: C12, C14, C16 and C18 in CHES buffer, pH 10. Upon heating, DSC shows that the C12, C14 and annealed C 16 lipids undergo a single transition which XRD shows is from a lamellar, chain ordered subgel phase to a fluid phase. This single transition splits into two transitions for C18, and FTIR shows that the upper main transition is predominantly the melting of the hydrocarbon chains whereas the lower transition involves changes in the headgroup ordering as well as changes in the lateral packing of the chains. For short incubation times at low temperature, the C 16 lipid appears to behave like the C18 lipid, but appropriate annealing at low temperatures indicates that its true equilibrium behavior is like the shorter chain lipids. XRD shows that the C12 lipid readily converts into a highly ordered subgel phase upon cooling and suggests a model with untilted, interdigitated chains and an area of 77.2 angstrom(2)/4 chains, with a distorted orthorhombic unit subcell, a = 9.0 angstrom, b = 4.3 angstrom and beta = 92.7 degrees. As the chain length n increases, subgel formation is slowed, but untilted, interdigitated chains prevail. (c) 2004 Elsevier Ireland Ltd. All rights reserved.
• Hachisako, Hiroshi; Yamazaki, Tetsuya; Ihara, Hirotaka, Journal of the Chemical Society. Perkin transactions II, 1994, # 7, p. 1671 - 1680
  作者：Hachisako, Hiroshi、Yamazaki, Tetsuya、Ihara, Hirotaka、Hirayama, Chuichi、Yamada, Kimiho

  DOI：——

  日期：——
• Preparation of gemini-type amphiphiles bearing cyclitol head groups and their application as high-performance modifiers for lipases
  作者：Yurie Mine、Kimitoshi Fukunaga、Ken-ichi Samejima、Makoto Yoshimoto、Katsumi Nakao、Yoshiaki Sugimura

  DOI：10.1016/j.carres.2003.12.006

  日期：2004.2

  Five gemini-type amphiphiles bearing cyclitol head groups, which have abundance of axial hydroxy groups, are newly synthesized. The syntheses are based on a common mixed anhydride method utilizing N,N'-[iminobis(trimethylene)]bisquinamide, prepared from iminobispropylamine and quino-1,5-lactone, and dialkyl N-(3-carboxypropanoyl)-L-glutamates as polar and hydrophobic components, respectively. Candida rugosa lipase (CRL) and Pseudomonas cepacia lipase (PCL) are co-lyophilized with these synthesized gemini-type amphiphiles, and their transesterification activities in organic solvents are evaluated. The modified PCL and CRL prepared by using each amphiphile showed highly enhanced and moderately enhanced enzyme activity, respectively. These results are discussed in terms of the increased preferential exclusion of the hydrophilic heads of the amphiphile and of the topological view of the amphiphile. (C) 2003 Elsevier Ltd. All rights reserved.